A lil context: our party (of around 5) had been captured by drow and abandoned a small island inhabited by humans, goblins, and orcs. We decided to approach the orcs to see if they would aid us in taking out the drow and get off the island. I play a female half-elf paladin, while my friend plays her twin brother. Our campaign has been run using milestone levelling, rather than XP for story reasons.
Orc Leader: by our custom to gain our loyalty, you must compete to show your physical prowess!
(DM tells us to roll Athletics or Performance to see which of us will be picked for the trial)
Me: rolls nat20 Athletics
Twin: rolls nat20 performance
Orc Leader: you! The small double-elf persons! You shall compete in our physical challenge!
Twin: *leaning into the orc’s space* what kind of physical challenge, big boy? Surely we can bend the rules a little.
Me: I wink flirtatiously.
DM: Make a persuasion roll, with advantage because of your sister
Twin: rolls nat19
DM: Seriously? *rolls a nat1 for the orc’s saving throw* oh come on!
Orc Leader: (nervously) Crekkar accepts your challenge!
DM: And so you both take Crekkar to his tent and show your …physical prowess. *rolls dice* You both tire him out easily while you remain almost unaffected. The orcs appreciate your strength and endurance and are now your allies.
Me (ooc): *jokes* level up!
DM: … actually. I had planned for the milestone to be after you conquered the orc camp, either by killing them or proving yourself in combat. So, yeah. The entire party is now level 3.
Monk: I can’t believe I can now catch arrows because the twins are sluts